Synthesis 2020; 52(15): 2190-2195
DOI: 10.1055/s-0040-1708017
© Georg Thieme Verlag Stuttgart · New York

Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate: New Developments

Alexander Safrygin
Saint Petersburg State University, Saint Petersburg, 199034, Russian Federation   Email:
› Author Affiliations
This research was supported by the Russian Foundation for Basic Research (project grant 18-33-00016). Alexander Safrygin is grateful to Saint Petersburg State University for providing his postdoctoral fellowship.
Further Information

Publication History

Received: 05 March 2020

Accepted after revision: 26 March 2020

Publication Date:
16 April 2020 (online)


The earlier described reaction of homophthalic anhydrides with aromatic ketones and ammonium acetate was tested for cyclic ketones (yielding spirocyclic motifs) and aliphatic aldehydes. In contrast to previous findings, the reaction was found to require no catalyst at all and to be applicable, in the non-catalyzed format, to these new carbonyl substrates as well as aromatic ketones. The reaction typically proceeds with high diastereoselectivity; if not, the initial diastereomeric mixture can be quantitatively equilibrated into a single, trans-diastereomer on treatment with aqueous base.

Supporting Information

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